Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation

The first iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(i)/phosphoramidite complex, makes use of the latent enolate character of an α...

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Detalles Bibliográficos
Autores principales: Sarkar, Rahul, Mukherjee, Santanu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179414/
https://www.ncbi.nlm.nih.gov/pubmed/34164076
http://dx.doi.org/10.1039/d0sc06208a
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author Sarkar, Rahul
Mukherjee, Santanu
author_facet Sarkar, Rahul
Mukherjee, Santanu
author_sort Sarkar, Rahul
collection PubMed
description The first iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(i)/phosphoramidite complex, makes use of the latent enolate character of an α,β-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its α-position in a branched-selective manner in moderate to good yield with good to excellent enantioselectivities (up to 98 : 2 er).
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spelling pubmed-81794142021-06-22 Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation Sarkar, Rahul Mukherjee, Santanu Chem Sci Chemistry The first iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(i)/phosphoramidite complex, makes use of the latent enolate character of an α,β-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its α-position in a branched-selective manner in moderate to good yield with good to excellent enantioselectivities (up to 98 : 2 er). The Royal Society of Chemistry 2021-01-15 /pmc/articles/PMC8179414/ /pubmed/34164076 http://dx.doi.org/10.1039/d0sc06208a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Sarkar, Rahul
Mukherjee, Santanu
Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title_full Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title_fullStr Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title_full_unstemmed Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title_short Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
title_sort iridium-catalyzed enantioselective olefinic c(sp(2))–h allylic alkylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179414/
https://www.ncbi.nlm.nih.gov/pubmed/34164076
http://dx.doi.org/10.1039/d0sc06208a
work_keys_str_mv AT sarkarrahul iridiumcatalyzedenantioselectiveolefiniccsp2hallylicalkylation
AT mukherjeesantanu iridiumcatalyzedenantioselectiveolefiniccsp2hallylicalkylation

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